This story originally appeared on the Gents Cafe Newsletter. You can subscribe here.
I have briskly strode the streets of Old San Juan on many occasions, I have sauntered through them but once.
This 500-year-old city can be just as easy to hate as it is to love. If you only look at the surface, the city’s whimsy runs no deeper than the pastel paint adorning its Spanish colonial buildings. To truly love La Ciudad Amurallada, one must first scale its stone walls and look beyond its many blemishes; and, frankly, this is impossible to achieve without first surrendering to “island time.”
Old San Juan is not a city that cares to deliver on your expectations. She is the oldest colonial city in the Americas – y ella ha bailado la Bomba con otros pretendientes. If she invites you within her walls, you must dance her Bomba, on her time.
The first sung note of la Bomba – a perfectly brewed latte at Cuatro Sombras – I stumbled upon because the cafe I initially wanted to go to did not open. When you dance with this city, she takes the lead.
Caffeinated and satiated, it is time to explore. The next stage of la bomba is for the dancers to enter the circle and promenade – promenade I do. Old San Juan is not a city to be driven through. The old, narrow streets do not accommodate the gear head and his toys. Perhaps a playful Suzuki SJ413 convertible would do alright in these parts, but not like a well-fitting pair of shoes. Alley cats patrol their turf with attentive discretion. Patio tables, never accompanied by more than two chairs, manage to find scraps of shade around westward corners. Here visitors and locals alike have found the perfect location for a midday imbibement.
A cruise ship in the distance emits 3 thunderous blasts from its horns – horns that make a train whistle sound about as intimidating as a kazoo. These are a sailor’s salute to the band in acknowledgement that once again la bomba has begun for them.
The music begins to crescendo now. It cuts through the familiar bustle of a metropolis as the sun descends into the ocean. I stroll into El Jardin de Princessa, a small park outside the city walls. The vegetation softens the outside clamor of the city, all that can be heard in this tranquility is the music of a lone street saxophonist playing slow and steady jazz. He is joined in song by the Common Coqui, a frog miniscule in stature but deafeningly loud. The setting sun casts shadows from the trees while they sway in the wind – the city opens herself, ceremoniously, to finally follow my lead in this dance.
I work my way towards La Casa de Montecristo, a popular cigar lounge where a newfound friend, Eduardo, will be playing jazz with the others in his quartet. A 3-time Latin Grammy nominee, he plays in venues across the island with great regularity. A reserved table awaits me inside, I tour the expansive selection of cigars and settle on a very mild “Short Perfecto” by Davidoff. An order of drinks follows.
Conversations in varied languages echo loudly throughout the room, yet all who are present share the common tongue of the drunkard. The dialogue begins with a pina colada (invented just around the corner at Barrachina), a response comes in the form of a tall mojito, tequila shots interject, sipping rums play the wallflower, and I sit contently coming and going into conversation with the crisp charm of a gin and tonic.
The band starts to play and now the dance is in full swing. A bouncy melody whirls through the smoke-filled haze of the cigar lounge. In every corner and at every table are lovers, dreamers, romantics, and closeted artists of some form or fashion.
The subtle red flame edges its way through the tobacco wrapping of my cigar, resembling lava flowing down an erupting volcano. Roaring bongos complete the fantasy, a fitting tribute to El Yunque – the towering, mountainous rainforest at the center of the island and once the supervolcano Hato Puerco that birthed her.
Eventually the dance must end. I tip the subidor (or in my case Eduardo and his band), bow to the crowd (stumble home amidst the other drunks), and take leave of the stage. It is time to retire my shoes for the night, resting my weary feet after their cobblestone-constitutional, and prepare for tomorrow’s dance.
